10 Creative Questions for First Dates
Dates can be nerve-wracking. The bad ones can feel like a job interview; the really bad ones can feel like interrogations. If you go on enough dates, you find yourself repeating the same stories over and over again. At a certain point, it might be more convenient to simply hand a brochure – a personal mini-Wikipedia page – where your date can go through all the basic details and then you can finally get to the nitty gritty.
This doesn’t have to be the case. You don’t need to stay stuck on surface level topics where you run through what you do, where you’re from, and what your favorite movies are. The truly magical dates are ones where you get lost in conversation, follow all sorts of tangents, and only after hours of back and forth do you realize you don’t even know what the other person does for a living.
While there’s never a guarantee that you’ll get there (there are so many other factors like natural chemistry), there are questions that can nudge you in that direction. Here are ten that you might want to keep in your back pocket next time you meet someone new:
What’s a common trait shared by everyone you’ve dated?
Here’s an alternative to the typical “what’s your type?” question. While that question isn’t necessarily bad, often people can draw a blank. Maybe they don’t think they even have a type. Now, if you ask them for a common denominator between their exes, then there’s a clear path to an answer. It could be fun to find if there are recurring patterns – both good and bad.
Think back to who you were ten years ago. In what ways does your younger self make you cringe?
This question is a fun way to get a sense of how much a person has grown. I mean, if someone says nothing they did in their youth makes them cringe now, have they grown at all? Or are they stuck pining for their so-called glory days?
If you never had to sleep ever again, how would you spend all that extra time?
Go beyond asking what a person does to unwind. (I mean, a big chunk of us, having been exhausted after a long day of work, probably just plop down on the couch and rewatch Brooklyn Nine-Nine for the ninety-ninth time.) Instead, ask them what they would do with a sudden surplus of time. Maybe they’ve always wanted to learn Portuguese. Or perhaps they’ve long wished to pick up the saxophone again. Or maybe they have a novel in their head just waiting to be written.
What disclaimers do you have to give before someone decides to live with you?
On first dates, we’re told to put our best foot forward. This is perfectly fine but you’re not going to fall in love with just that foot, are you? If you want to assess someone as a potential partner, you’re going to look at everything. Rather than simply asking them about their flaws, see if they’re self-aware enough to know in what ways they might be a grating roommate. Find out who’s the messy one in the relationship, or who stays up til 3 in the morning tapping away at the great American novel.
In what ways are you privileged?
Once again tapping into self-awareness, it can be incredibly eye opening to suss out what a person believes about privilege. Do they know about how society might have made their life systemically easier or harder? Do they believe they’re completely self-made or can they acknowledge the ways the path has been paved for them? The thing is everyone is privileged is some form or another. Knowing that is essential to stay both grounded and grateful.
Ten years into a relationship, would you rather haveintimacy without commitment or commitment without intimacy?
Here’s a spicy one. Besides the fact that friendly debate is a great way to get a conversation going, this question specifically gets you to talk about what you believe about exclusivity, how you define intimacy, and so on. You also get a chance to talk about what you expect out of a long-term relationship.
Name one issue, whether bigor small, that you think you could contribute to solving.
On first dates, there’s a tendency to get stuck in a loop of sharing biographical details. You go back and forth talking about your selves, how great you are, and why you deserve to go on a second date. This question is an effective way of getting out of that and steer the conversation towards the bigger picture. Rather than talking about your dreams and what gives you a sense of fulfillment, talk about what role you play within the context of your community. See what causes they’re passionate about or if there any issues they care about in the first place.
Would you rather give your past-self advice or ask your future-self a question?
Here’s another friendly debate question that explores both regret and anxiety. No, they’re not necessarily sexy topics, but you get to learn about their upbringing on a much deeper level. If they want to give their past-self advice, what advice would that be? What do they wish they had done differently? And if they would rather ask their future-self a question, you can see what they tend to worry about. By discussing this question, you can discern how similar or different you tow are in terms of values and perspective.
How has your definition of love changed since your first relationship?
Once you’ve been through the ringer, you’re bound to change your views of love and romance. Whether it’s shaped by your parents’ marriage or by Disney films, you probably got into your first relationship with a specific idea of what love is supposed to look like. By asking this question, you get a glimpse of this person’s journey. In what ways have they hurt and been hurt? What have they learned from heartache? Does their definition of love match yours?
Do you believe chemistry is inherent or is it something you can build over time?
Finally, here’s one that’s a bit meta. Whether you believe chemistry is discovered or developed, the mere discussion can open up a whole can of worms. Do they expect conversation between partners to always feel effortless? If you lose that spark with a partner, is it a sign that it might be over, or does it simply mean you need to work harder? Lastly, asking this can naturally lead to the question of, “Well, do you think we have chemistry?” which could be a fantastic way of asking, “So when’s our next date?”
Well, there you go. While I can’t guarantee these will lead to a second date – let alone a relationship – I will bet they would at least make your time together much memorable.
If you enjoyed these questions and want more, why not order the More Than Friends deck? This collection contains over fifty questions and prompts for both established couples and potential partners.